Updated 1:11 pm, Tuesday, July 15, 2014

Created with ample sophomoric humor, the men’s and women’s clothing on offer from Betabrand is intentionally gimmicky, but that’s exactly what appeals to fans who routinely upload images of themselves in company gear to the website and participate in the brand’s latest marketing experiments. With a retail outpost in the Mission District, Betabrand’s increasing focus on crowd-sourcing of design ideas and crowd-funding them into production makes it possible to release new products each week.

Why it’s addictive: Thanks to the crowd-funding model that saves shoppers more when they back product concepts early on, it’s possible to save up to 30 percent if you’re one of the first in line to support a new design. www.betabrand.com

There’s a sleek, refined quality to the unfussy staples you’ll find at Everlane, among them silk button-downs, denim shirts and cashmere pullovers for $60-$78. Bypassing the traditional wholesale retail model, the company, founded by Michael Preysman, designs and produces its own apparel and then sells it direct to consumers to keep prices lower than department store equivalents.

Why it’s addictive: Classic basics with a tinge of heritage styling make these pieces that will easily land at the core of your wardrobe. www.everlane.com

A subscription service offering shipments of jewelry and accessories that can be worn for as long as you like, kept and purchased or returned for a new set.

Le Tote ships boxes packed with three pieces of jewelry ($19/month) or a mix of five apparel and jewelry items ($49/month) from 40 youthful, contemporary apparel and jewelry labels (BB Dakota, Kensie and French Connection) for the girl who craves a constantly refreshed wardrobe on a budget. Love something you receive? Buy it for less than retail. Send the rest back for your next shipment.

Why it’s addictive: The appeal of always having a new, trendy item to wear with seriously minimal effort. www.letote.com

By all accounts, wearable technology has a long way to go before it can claim to have won the hearts of fashion fans. But Misfit Wearables’ Shine hints there may be hope yet. Delivering a heretofore unseen dose of style to the self-quantified movement, the wearable tracker not only works in socks, on the sleeve of a workout tee and with a leather band, but it can be worn as a necklace and comes in hues such as coral and sea glass.

Why it’s addictive: With more than one way to wear it and an array of options for doing so, the Shine stands out for giving self-quantifiers a range of aesthetic choices. www.misfitwearables.com

An online-only brand whose playful, retro-minded style has evolved from its co-founders’ high school side project into a e-commerce juggernaut with over 1.1 million fans on Facebook and annual revenue of over $100 million.

Anyone who says San Francisco doesn’t have a stake in fashion clearly hasn’t pondered the city’s plethora of born-online brands. At the top of the pyramid, there’s ModCloth, whose social media-savvy approach to selling fashion and experiments letting customers determine what women’s apparel it will sell next has built the company started by co-founders Susan Gregg Koger and Eric Koger — high school sweethearts who are now husband and wife — into a brand that releases up to 50 new products each day, counts over 500 employees and $48 million in venture capital.

Why it’s addictive: Along with being a go-to for vintage-inspired apparel and accessories, the company wins applause for successfully letting fans choose what it sells and integrating plus sizes and models into its core marketing. www.modcloth.com

What: The social network for sharing images that spawned countless copy cats and was most recently valued at $5 billion.

Fashion is more visible, shareable and viral than ever, thanks in large part to its presence as a core part of what populates Pinterest, the San Francisco company best known for making scrolling walls of images a constant and a norm of today’s online experience. The hotly anticipated rollout of paid advertising this spring through Promoted Pins stands to make the network even more attractive to brands.

Why it’s addictive: The network’s increasing popularity among consumers, as well as the confluence of brands and retailers using it as a marketing tool, have made it a choice place to discover the latest styles, new product launches and plenty of behind-the-scenes glimpses of designers, labels and fashion icons. www.pinterest.com; read more about Pinterest here.

Limited-edition, on-trend micro-collections featuring three coordinating items sold at a bundled price that’s lower than the total of what each would cost individually.

Instead of a full collection launched seasonally, tech-savvy upstart PopBasic designs and produces a trio of items and releases them in limited editions that typically sell out. For $85, the label’s recent Paloma collection delivered a basic white T-shirt, iPad-size gray leather clutch and a lightweight, striped infinity scarf in coordinating gray. PopBasic’s first permanent item, the Le Breton long-sleeve striped T-shirt added this spring, signals expansion, as well as its emphasis on easy, versatile basics.

Why it’s addictive: An avenue for stylish basics, there’s the sport of snapping up collections before they sell out. Free worldwide shipping is an attractive perk for the company’s sizable cadre of overseas fans. https://popbasic.com

A social Web and mobile platform for buying and selling new and gently used apparel and accessories.

Proving that shoppers will not only willingly buy and sell using their smartphones, but will do so obsessively is part of Poshmark’s claim to fame. Some sellers report having made as much as $80K through the Bay Area startup’s app, which offers access to over 400,000 virtual, shoppable closets stocked with more than 7 million items. With $15.5 million in funding from investors that include Rachel Zoe and Ashton Kutcher, the company reports tenfold growth in 2013, with the average member spending between 20 and 25 minutes on the platform per day.

Why it’s addictive: A strong community of Poshers who open the app multiple times a day and frequent in-app Posh Parties that draw people to shop different themes simultaneously make the buying and shopping experience here addictively social. https://poshmark.com

Pictured: Lauren Smith photographs jewelry for her profile on Poshmark.

Luxury online consignment site for scoring Chanel, Prada, Gucci and many others at up to 90 percent off.

There are many places to buy and sell secondhand apparel and accessories online today, but founder Julie Wainwright’s laser-like focus on coveted, high-end brands has made the RealReal the go-to for luxury consignment, on track to do $100 million in revenue this year. Investors have dropped $43 million in funding to date to grow this company’s ever-expanding selection of apparel, accessories and handbags from the likes of Chanel, Hermès, Louis Vuitton and others.

A jewelry subscription service that lends you a set of three accessories picked just for you for up to 60 days.

An endless array of accessories becomes more than just a daydream with RocksBox, which lends subscribers who pay $15 to $19 a month three items of jewelry matched to their personal style profiles. Well beyond its bootstrapped beginnings, when founder Meaghan Rose even lent out her own jewelry to get her idea off the ground, the service now features a collection of statement-makers and everyday pieces from House of Harlow 1960, Samantha Willis, Margaret Elizabeth, CC Skye and many others — all available for purchase to subscribers at 20 percent off retail.

Why it’s addictive: Every box is a surprise, and you can pick and choose how long you keep each one. Obsessed? Wear your items for weeks. Not so much? Send ’em back for a new set. www.rocksbox.com

A Web and mobile tool for tracking when items from brands you love go on sale.

A serious time- and money-saver for shoppers who know the brands that work best for them, Shop It to Me, founded in 2005 by Charlie Graham, combs the Web and alerts its 4 million-plus members when apparel and accessory items from about 100 major retailers – from Barneys to Shopbop and Intermix — go on sale. Along with its core “salemail” e-mail alerts, an iPhone app lets you refine your feed of daily deals on the go.

Why it’s addictive: A ton of flexibility. “Heart” individual items to receive price drop alerts or set up notifications for specific brands, sizes and price ranges. Also works with menswear and children’s apparel, making it possible to monitor deals for yourself and others in one place. www.shopittome.com

What: With over 7.5 million users, this iPhone and Android mobile app offers rewards, called “kicks,” for simple in-store activities — starting with just walking in. Accrued kicks can be redeemed for gift cards, products or donated to charity.

Ranked the most-used real-world shopping app this year by Nielsen, ShopKick has already helped make it more common for shoppers to browse in stores with phones in hand. The company’s newest venture is likely to make an even bigger impact. First beta-tested in Macy’s stores in San Francisco and New York, the new ShopBeacon service uses Apple’s iBeacon technology to deliver location-specific deals, rewards and recommendations to shoppers in stores while they browse.

Why it’s addictive: As long as you remember to open the app before you enter the company’s 15 participating national retailers, a list that includes Macy’s and Target, you’ll earn rewards for things you’d do anyway, like walking in to browse or scanning products for more information. www.shopkick.com

What: Personal shopping in box form, each “fix” contains five items you can try-on at home, return or buy.

From its 2011 beginnings in founder and CEO Katrina Lake’s apartment during her final spring at Harvard Business School, Stitch Fix has since shipped hundreds of thousands of fixes packed with a mix of five apparel and accessory items chosen by company stylists. High-level hires from Walmart.com and Netflix have helped the company leverage technology to put the right items in the right customer’s boxes to max sales and keep fans coming back for more. The company reports that 70 percent of its clients request a second fix within 90 days of their first.

Why it’s addictive: Starting with an online style quiz when you sign up, the service is personalized from the get go, but designed to get better over time as stylists review your past purchases, buying habits and special requests. www.stitchfix.com

What: Both a marketplace for cool, design-driven finds and a solution for small retailers seeking an inexpensive way to set up shop online.

Home to a serious repository of stylish goods from small, independent brands, Storenvy is fast-emerging as a favorite among both shoppers and makers. It’s easy to see why: Creators of everything from artisan soaps to hand-hammered jewelry and graphic tees can create custom online shops for free, while browsers get access to personalized product feeds filled with one-of-a-kind apparel, accessories and homewares.

Why it’s addictive: With over 85,000 independent retailers on the platform and 800 new stores added each week, we dare you to walk away from a browsing session here without a new item or two on your wish list. www.storenvy.com

A website that allows locals to rent dresses from other women’s closets.

For special occasions, there’s Style Lend, stocked with night out-worthy dresses you can borrow from another San Francisco-dweller’s closet for as little as $15 a week. You know those dresses you aren’t quite ready to part with but won’t wear again anytime soon? List them here to earn 50 to 70 percent of the rental fee, depending on whether you deal directly with renters or hand that task over to the company.

Why it’s addictive: You can earn passive income from the clothes hanging in your closet and find a new look for an upcoming event without buying a new dress you know full well you’ll only wear once. http://stylelend.com

A site for booking hair, beauty and skincare appointments with roughly 200,000 professionals in cities around the country.

Anyone who’s tried to find a compatible hair stylist or aesthetician in a new town quickly understands the beauty of StyleSeat, whose platform gives beauty-seekers a way to search profiles and book appointments online or via smartphone for free. The new client deals offered by many stylists bring added ways to save, while images uploaded by its most active hair stylists, and nail and makeup artists provide a never-ending source of inspiration, whether you’re looking for wedding hair ideas or just brainstorming your next mani pedi color strategy.

Why it’s addictive: Online scheduling frees you up to book appointments during office hours without everyone nearby knowing your “lunch meeting” is really a Brazilian. www.styleseat.com

Pictured: Melody McCloskey, CEO and co-founder of Styleseat, is seen at the Styleseat offices in San Francisco, Calif.

An iPhone app that determines your bra size using computer vision technology (don’t worry, it only sounds creepy), then lets you shop its collection of bras, panties and loungewear. (Coming soon to Android)

Power up Third Love’s slick iPhone app to accurately size yourself using the camera on your iPhone. Step-by-step instructions guide you through the process, from what to wear (a tank top) for accurate measurements to how to position the camera. Along with the industry sizes you’re already familiar with, Third Love’s collection also sells cups in half-sizes exclusive to the company and allows shoppers to customize bra colors and trims. Options range from a practical memory-foam “24/7” bra fit-tested on hundreds of women in sizes A through F to balconet and plunge bras in colorful lace.

An online beauty store where you can try toxin-free beauty brands before you commit to buying.

Trymbl makes it easy to discover new beauty products free of toxins with its try-before-you-buy online service, which gives members access to trial- and full-size cosmetic and skincare products. These can be tested for up to 15 days and then purchased or returned, no questions asked.

Why it’s addictive: Discovering new skincare and beauty products can be challenging and costly endeavors, especially when it comes to new and emerging brands without tons of online reviews or availability in department stores. While subscription boxes such as Birchbox have long offered samples of mainstream products, Trymbl’s toxin-free focus is a boon for anyone interested in cutting chemicals from their beauty routine. http://www.trymbl.com

An online shop that determines your bra size using an algorithm-driven quiz, then lets you try on up to five selections at home, risk-free.

Lingerie shopping has gotten a long overdue tech upgrade thanks to San Francisco startups True & Co. and ThirdLove. With a new in-house collection just out, the e-commerce company’s online questionnaire is designed to take two minutes and rival the accuracy of a human fitting specialist. Next, shoppers can try up to five bras and five other items from the shop — a total of 10 styles altogether — at home for free. Brands include popular labels such as Calvin Klein, Natori, Honeydew and Spanx, which are featured alongside the company’s in-house collections.

Why it’s addictive: No more awkward bra-fitting experiences in dressing rooms, plus the efficiency of trying on five styles at home. https://trueandco.com

A Pinterest-like Web and mobile platform for discovering and buying products from over 300,000 stores.

You’d never guess Wanelo founder Deena Varshavskaya struggled for more than two years to gain traction for her company — whose name is a mashup of Want, Need, Love — before becoming one of the city’s most-watched startups, with over 11 million users and $14 million in funding from Floodgate Fund, First Round Capital, Forerunner Ventures, Naval Ravikant and others. Especially hot with young women, the site connects its more than 11 million members with an endless array of products they can buy, save to collections or share — activities they will soon be able to do at 100-plus Nordstrom juniors departments, which will display the retailer’s Wanelo page on screens for in-store shoppers.

Why it’s addictive: Like Pinterest, it’s set up as a grid of scrolling images. Unlike Pinterest, everything you see is available for purchase — until it sells out, of course. https://wanelo.com

It was once novel to talk about the intersection of fashion and technology, but today it's surprising we ever thought it might be otherwise. After all, technology is changing everything we do - from driving to genotyping. Why shouldn't it change fashion, retail and shopping, too?

Fashion is also changing technology, and the Bay Area is at the center of this revolution in the way we discover, share and consume fashion (among other products). Some of the world's biggest technology companies are now bringing in fashion veterans like former Yves Saint Laurent CEO Paul Deneve and Burberry CEO Angela Ahrendts (Apple), partnering with designers like Diane von Furstenberg (Google), and betting on acquisitions, including a 3-D virtual-fitting technology company (eBay), to secure long-lasting style cred among a wider audience.

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With the number growing by the day, the time was right to select the 20 Bay Area companies who are redefining fashion and technology. Our picks - many seasoned, others brand-new - all exhibit impressive growth, new technology, savvy marketing or just good, old-fashioned problem solving. They've captured our attention - we think they deserve yours, too.

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